Captain Skylar
US Coast Guard Captain, Certified Sailing Instructor & Licensed Oregon Outfitter
I grew up in Brookings, Oregon, working at the port and listening to sailors tell stories from the sea. Their adventures stayed with me, and in 2016 I moved to San Francisco to begin my own sailing journey. I still remember one of my first classes, two reefs in the main and short-tacking up Raccoon Strait in the rain. Cold, soaked, and smiling the whole time. I was hooked.
Since then I have trained through advanced offshore courses, earned my USCG Master Captain license, and became an ASA Instructor. I have sailed up the coasts of California and Washington, explored the San Juan Islands, and as a member of the Columbia River Sailing Association I have sailed to many destinations along the Columbia River. I have also taken my own boat safely across the Columbia River Bar. These experiences taught me to stay curious, stay prepared, and respect the water.
Outside of sailing I have worked as a Licensed Professional Counselor, public school teacher, and ESL instructor abroad. These paths taught me the value of authenticity and connection, which I bring to every sail.
What I love most about sailing is that it is never the same twice. It demands focus yet still feels freeing. My philosophy is simple, if you are not having fun, you are doing it wrong. At SkyWind Sailing my goal is to share that joy and sense of adventure with everyone who steps aboard.
James
First Mate
James grew up in Portland and only discovered the local sailing scene a few years ago. Since then, he has been on the water several days a week, racking up enough hours to qualify for his captain’s license. At this point, it is just the paperwork that remains. You might spot him tagging along on a class or charter, lending a hand and sharing in the fun.
Before catching the sailing bug, James was an avid marathon runner, and he brings that same endurance and focus to every voyage. These days, the only finish line he is interested in is the horizon. When he is not on the water, James works as a licensed clinical pharmacist, balancing precision and care in both his professional and sailing life.
Scuttle
Treat Officer
Scuttle might not be the biggest fan of sailing when the boat is heeled over, but he has carved out his own role as the crew’s resident comfort seeker. He much prefers calm days on the water, curled up in a blanket, or weekends lounging on the docks at Government Island where there are plenty of people to greet and treats to sniff out.
Even though the sport is not his first love, Scuttle has still logged some serious miles, sailing all the way from Portland, across the treacherous Columbia River Bar, to the San Juan Islands and back. With that kind of journey under his collar, he has truly earned the title of a salty dog.